Water → 4-[4-(3-Dimethylamino-benzoylamino)-phenyl]-butyric acid ethyl ester

HRID 1023700

반응식

HRID 1023700 반응식
[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH2:13]([O:15][C:16](=[O:27])[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1)[CH3:14].C(N(CC)CC)C.O>C1COCC1>[CH2:13]([O:15][C:16](=[O:27])[CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([N:2]([CH3:12])[CH3:1])[CH:4]=2)=[CH:24][CH:25]=1)[CH3:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 70103423-Dimethylaminobenzoyl chlorideHCID 10013251Ethyl 4-(4-aminophenyl)butanoate

생성물 1

HCID 670453314-[4-(3-Dimethylamino-benzoylamino)-phenyl]-butyric acid ethyl ester수율 97.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 3-dimethylaminobenzoyl chloride (0.19 g, 1.01 mmol) in THF (6 ml) was added dropwise to a solution of 4-(4-aminophenyl)butyric acid ethyl ester (0.26 g, 1.24 mmol) and triethylamine (0.31 g, 3.11 mmol) in THF (8 ml) under ice cooling. The reaction solution was stirred at room temperature for 8 hours, then added with water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous ammonium chloride and saturated brine, then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=15:1) to obtain 4-[4-(3-dimethylamino-benzoylamino)-phenyl]-butyric acid ethyl ester as a brown oily substance (0.36 g, yield: 97.5%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous ammonium chloride and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=15:1)

출처 및 근거

ORD 기록
ord-537ee15699e143968a5b63286d5a401a
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722723B2

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